


Vacation with Curly!

by Triestowritenovels99



Category: The Outsiders - All Media Types, The Outsiders - S. E. Hinton
Genre: Attempt at Humor, Cute, M/M, Mild Language, Summer Vacation
Language: English
Status: In-Progress
Published: 2021-02-01
Updated: 2021-03-07
Packaged: 2021-03-18 10:21:30
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 5
Words: 2,548
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29116683
Author URL: https://archiveofourown.org/users/Triestowritenovels99/pseuds/Triestowritenovels99
Summary: Darry decides to take his brothers on vacation. The problem? A lovesick Curly is tagging along, much to Darry's displeasure.
Relationships: Ponyboy Curtis/Curly Shepard
Comments: 2
Kudos: 52





	1. Vacation!

**Author's Note:**

> This is my third fanfiction. 
> 
> Any type of feedback would be appreciated!

Ponyboy felt someone shake him softly. He stirred in his sleep, but didn't wake up. All he did was roll onto his stomach. The person shook him harder, obviously wanting him to wake up.

"Mmmm,"he groaned in his sleep.

"Ponyboy. Ponyboy, wake up." It was his brother, Sodapop. Ponyboy didn't care, he just wanted to sleep.

"No, let me sleep."

"Come on, Pones. Darry wants to tell us something." Ponyboy let out a sigh. He sat up, slowly opening his eyes.

"Fine. Just let me get dressed." Sodapop left the room, probably heading for the kitchen. Ponyboy got up and gathered some clothes. He showered and did his other daily rituals.The most important one was greasing his hair. He was no longer a blond, but an auburn. The bleached hair was long gone.

After getting ready, Ponyboy headed for the kitchen. There was a plate of eggs, bacon, and toast at where he sat. His oldest brother gave him a nod, eyes still on the newspaper. Ponyboy sat down, and started to eat.

After breakfast, Ponyboy helped with the dishes. Sodapop helped dry them. Darry was still sitting at the table, most likely he was gonna tell the news in here. Ponyboy hoped it was good. It's been awhile since there was any good in his life. Not ever since there deaths.

Ponyboy and Sodapop sat across from Darry. All the dishes were dried and put away. Ponyboy tapped his fingers on the table, getting impatient. He wanted to know what Darry was gonna tell him.

"Darry, what were you gonna tell us?" Ponyboy asked after a few minutes of silence. Darry finally set his newspaper down and eyed both his brothers. He cleared his throat to speak.

"You know how I have been working extra the past few months?"

"Yeah, Darry. You have been working really hard." Sodapop said with sympathy.

"Well, I have been saving up, and I finally have enough. How do you boys feel about going on vacation?"

"Vacation!?" Both brothers said in unison.

"Yes, we're heading to Florida!" Sodapop stood up and did a little dance and cheeree Ponyboy had a smile from ear to ear. A vacation was definitely good news.

"Darry? Are Steve and Two-bit coming?" Ponyboy asked after some of the excitement wore off. Darry shook his head no.

"Just us, it is a trip so we can bond. As brothers. Now I'm gonna head to the store, we need a few things for the trip. Don't get into any trouble while I am gone." With that, Darry headed to his room to get ready. Sodapop got up too, headed to the door.

"Where are you going, Sodapop?" Ponyboy asked.

"To the DX, got to tell the boss I'll be gone for a week or so. Plus, I get to rub it into Steve's face. See ya later, Pones." With that, Sodapop headed out the door. Ponyboy was alone. If only Johnny was here, he would keep Pony company. Ponyboy got up, deciding he'd go to the park. Swinging was his new favorite place to daydream and let his thoughts go wild. He left a note to Darry and headed out the door.

However, he didn't know that he would have a run in with a curly haired greaser while he was out.

  
  
  
  
  
  
  
  
  
  
  
  
  
  



	2. Curly!

**Summary for the Chapter:**

> Ponyboy reunites with Curly.

**Notes for the Chapter:**

> I have chapter 2 done! 
> 
> Hope y'all like it. Feedback would be appreciated!

It was a very bright and sunny day in Tulsa, Oklahoma. It was definitely summer, most people were either swimming or in the shade of trees. Not Ponyboy. He was swinging, his eyes closed, not wanting to have his eyes hurt by the sunshine. He was daydreaming. Nothing in particular, just whatever came to mind.

Now, greasers and socs still didn't get along. It wasn't as bad, but the rich kids still harassed them whenever they could. That's why it was not a good idea to have your guard down. A soc could be anywhere. Or in Pony's case, a curly haired greaser.

Ponyboy was too lost in his head to hear the approaching teenger. He crept up onto Ponyboy and then…

"Hey!" A person yelled. Ponyboy was so startled that he jumped. Yes, he jumped off the swing, falling on the ground. He turned to glare at the person who yelled, until he saw who it was. Ponyboy let out a gasp.

"Curly! What are you doing here? I thought you were in the cooler?" Curly flashed him a toothy grin. 

"I got out with good behavior, baby Curtis. Now what are you doing all by yourself? And totally not aware. We don't want you to be on the back of a milk carton, do we?" Ponyboy rolled his eyes at this.

"There isn't anyone out here to kidnap me, Curly. Besides, nobody wouldn't want some grease like me." 

"Oh yeah, what if I kidnapped ya." Just for show, Curly went to pick up Ponyboy bridal style, causing Ponyboy to laugh.

"Put me down you dumb hood!"

"Hey, is that anyway to talk to ya elders?"

"You're only one year older, Curly."

"Still, you better learn respect boy." Curly did set him down and Ponyboy stuck his tongue out. Ponyboy then went back to his swing. Curly sat next to him. Curly pulled out a pack of smokes and took one out and lit it. He offered one to Ponyboy, but he declined. Curly took a drag on his cigarette and blew out smoke.

"I heard about Johnny and Dally. It must suck." Ponyboy swallowed a lump in his throat and nodded. He hated talking about their deaths. He was better, but not quite. He sometimes could remember them and smile. Other times, he would burst into tears, and either Darry or Sodapop comforted him. He felt himself starting to tremble. He then felt a hand on his shoulder. His eyes met brown orbs.

"I am not the best with this type of shit, but I'm here if you need me." Ponyboy gave a smile and nodded."So, what are you doing tomorrow, baby Curtis?"

"I actually am going on vacation. Darry is taking us to Florida."

"Can I come? I don't want to be stuck here all summer. Besides, my siblings can be annoying at times." 

"I don't know. Darry said it was just us brothers." Curly then did something that shocked Ponyboy. He gave him puppy eyes, which were oddly cute. Cute? Ponyboy couldn't believe he thought Curly was cute. But he was, in a rugged kind of way. Ponyboy let out a sigh. "Fine, I'll ask him. Just don't get your hopes up."

"Thanks, baby Curtis!" Curly pulled Pony's face and planted a wet kiss on his forehead. Ponyboy pulled back and wiped the spit off his face.

"That was nasty, Curly."

"It could have been nastier, babe." Curly said huskily. That caused Ponyboy to blush, red as a cherry. Curly let out a chuckle. "Anyways, I have to get going. See ya baby Curtis." Curly stomped his cigarette into the ground and sauntered off, leaving a confused Ponyboy.

"What just happened?" He whispered to himself. Not wanting to ponder on it, Ponyboy went back to swinging. Lost in his head again.

  
  
  
  
  
  
  
  
  
  
  
  
  



	3. Decision!

**Notes for the Chapter:**

> This is chapter 3!
> 
> Sorry if it's short, hopefully chapter 4 will be longer!
> 
> Any feedback would be appreciated!

As soon as Ponyboy entered his home, he went over to his oldest brother and gave him a hug. Darry returned the hug, wrapping an arm around his brother. He pulled back giving Darry an innocent look. 

"How was the park, Pones? You didn't get into any trouble did you?

"Of course not Darry. I know you'd ground me if I got into any trouble. It was fun. All I did was swing though."

"That's good. Keeps you out of trouble. Heck I'd be okay with you swinging until you're 30 if it keeps you in line." Darry then went back to his newspaper. Ponyboy stood awkwardly, not knowing how to ask his question. Really he was more worried about Darry's answer. They got along much better, but Darry still could be unreasonable. Ponyboy had to play it smart.

"Dar, can I ask you a question?"

"What is it?" Darry asked, not missing a beat.

"I wanted to ask if I could bring a friend on vacation? I know you said it was just for us, but I haven't seen my friend in a while."

"Do I know this friend?"

"Yeah. He goes to my school."

"What's his name?"

"Um, Cur-, Curt." Darry raised his eyebrow.

"The truth, Ponyboy."

"It's Curly. I know he has a reputation, but he's nice. Please, you will be there to make sure nothing happens. We'll be good, promise." Ponyboy gave Darry his puppy dog eyes. He let out a sigh.

"Alright. You've been good. Have good grades. But one mess up and you both will get it, savvy?" Ponyboy hugged his brother giving a kiss on cheek.

"Thanks, Darry! You won't regret this." Ponyboy then ran to his room, almost skipping. Darry shook his head, not sure about his decision.

His decision, that he would definitely regret.

  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  



	4. Long road ahead!

**Summary for the Chapter:**

> It's the day for them to head out. And Curly isn't the only one going...

**Notes for the Chapter:**

> Chapter 4 is here! Hope you all enjoy!
> 
> Any feedback would be appreciated!

It was the day of the trip. It was a bright and warm day. The sun was shining in all it's glory.The truck was packed with their suitcases, snacks for the long drive ahead, and anything else they may need. The three brothers were waiting on the porch. Waiting for Curly. Sodapop was angry that Ponyboy got to invite a friend. Well… Sodapop didn't invite anyone...

...Steve invited himself. 

He had arrived, a bag in his hand, wearing sunglasses on top of his head. Darry shot up from where he was sitting on the porch.

"Sodapop! I didn't say you could invite your friend. I already have to look after Curly and Ponyboy, but now Steve!? Are y'all trying to kill me before we even get there?"

"Relax, man. I invited myself. Besides, I can watch myself. I can't say the same for Ponyboy getting lost in his own head, let alone a different state." Ponyboy glared at Steve. "Curly? You might as well have bail money with you." This time, Ponyboy gave Steve the finger, causing Sodapop to smack him.

"I know. But he is Ponyboy's friend. I told them no funny behavior. Now where is Curly? Pones, do you know?" Ponyboy shook his head. Curly had his own schedule, he'd be here when he'd be here.

The gang decided to wait inside, leaving Ponyboy on the porch. Ponyboy was content with this, his head in the clouds. Thinking about what the trip would be like with Curly. He doesn't have many friends. His only best friend was Johnny. He didn't have anyone now. Maybe this trip could change it and he would get close with Curly. How close? He wasn't sure. Curly was often in the cooler. He could never stay out of trouble. 

Speaking of trouble. Curly was sauntering his way up to the gray eyed boy. A smirk on his face. He snuck up behind him. He wrapped his arms around him, causing Ponyboy to shriek. He pulled the boy close to him, causing the younger boy to blush.

"This is a weird way to greet someone, Curly. "

"If you were on a date with me, the greeting would be even weirder." Ponyboy blushed even more, turning red like a tomato. Ponyboy turned at an awkward angle so he could look at Curly. His eyes were a golden brown. Beautiful. Ponyboy shook away the thought, but it still hung in his head.

"You don't look ready for the trip, Curly."

"Yes I am. All I need is the clothes on my back. And you." Curly leaned in so close that their noses were touching. Ponyboy felt like he was going to melt. The door creaked open. 

"Curly Shepard! Get away from my brother!" Curly eyed Darry, not scared in the slightest. 

"Why? Not like we were doing anything. That's for the night." Darry knew what he was hinting at andgrowled. Curly let out a sigh and got up, but whispered in Pony's ear first. He headed over to the car, waiting. 

"What did he say, Ponyboy?"

"To make sure we have our own room. Away from the old man." Curly let out a laugh.

"You are so dead, Shepard!" With that Darry jumped off the porch, chasing after the curly haired greaser. Eventually Sodapop and Steve joined Ponyboy on the porch. All watching the spectacle in front of them.

"See Soda, this trip definitely won't be boring." Sodapop gave a nervous chuckle and Ponyboy rolled his eyes. This would definitely be a long trip.

A very long trip.

  
  
  
  
  
  
  
  



	5. Hotel!

**Notes for the Chapter:**

> Here is chapter 5! I hope you all enjoy! I want to say thanks for anyone who left kudos. 
> 
> Anyways any feedback would be appreciated!

The drive from Oklahoma to Arkansas was...interesting to say the least. Darry had to deal with Sodapop and Steve laughing and rough housing in the back of the truck. Curly, who kept on asking "are we there yet?" He clearly didn't know how far Florida was, Darry thought. Ponyboy was up front daydreaming. He wasn't bothering Darry, which was a plus for the oldest brother. 

Eventually, Darry stopped at a gas station. Everyone got out of the car, mainly to stretch. Steve and Sodapop clowned around. Curly stood close to Ponyboy. Talking to him in a whisper. Darry could see he was making Ponyboy blush. The brother didn't like it one bit.

After their break they were back on the road, knowing they'd need to find a hotel soon. The trio started late,thanks to Curly. By morning Darry was gonna try to drive straight to Florida.

"What did Curly say to you, Ponyboy?" Darry asked his brother. 

"Just stuff." Ponyboy said.

"What kind of stuff?"

"Bedroom Stuff. Like he hoped the mattress wasn't noisy." Darry slammed the break with his foot. Good thing no was on the road.

"You're dead!" Ponyboy held back Darry as he tried to reach back and strangle a laughing hood. A spectacle you'd see on a comedy show. 

"This is better than any movie I watched." Steve laughed. Sodapop nodded in agreement. 

Finally after a little more driving,(after Darry calmed down) they made it to a hotel. Darry got a room with two beds and a couch that pulled into one. Steve and Sodapop called the couch bed. Leaving the other ones for Darry, Curly, and Ponyboy to decide.

"You can have the bed to yourself, Dar. Curly and I can share." Curly smirked at the idea, which caused Darry to frown.

"I'm not so sure about that, Ponyboy. I don't really want you to be in a bed with  _ him _ ." He emphasized the word him. He hated the idea of them sharing a bed. Not with Curly having goo goo eyes on his kid brother. 

"It will be fine,Darry. You will be in here."

"Yeah old man, not like I'd try anything. That's for the beach, where lots of skin will show." Curly winked at Ponyboy, causing him to blush. Darry was about to see a different red. One of blood after he killed Curly. He let out a sigh.

"Fine, but no funny business, savvy?"

"Thanks, Darry!" Ponyboy said and hugged his brother. 

They stayed up a little, watching Mickey Mouse. Until it was bedtime. They headed in their respected sleeping area. Darry hated it. But what could happen in a hotel? While he was in the room? Nothing hopefully. 

But the balcony? Sounds like Romeo and Juliet.

And Darry's worst nightmare. 

  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  



End file.
